Meta Substitution Effect on Energetic Property and Aromatization of Some Acetophenone Derivatives: A DFT study

Abstract

The energetic properties and relative aromaticity of some derivatives of acetophenone structures were investigated in which the acetophenone was substituted by -NO₂, -CN, -Cl, -H, -CH₃ and -OCH₃ groups in meta position. For this purpose, density functional theory (DFT) calculations were applied using B3LYP/6-31+G(d,p) method. The results indicated that the aromaticity of the derivatives changed in the order of -NO₂ > -CN > -Cl > -OCH₃ > -H > -CH₃ for meta position. In addition, the results were directly related to the electron withdrawing and electron releasing strength and steric hindrance of substituents. The electrophilicity (w), HOMA, HOMED, aromatic stabilization energy, nucleic independent chemical shifts (NICS)(0) and NICS(1) indices of all derivatives were calculated and the results showed these descriptors have a nice correlation with Hammett constant.